1. Field of the Invention
The present invention relates to 5-acetoxy-(E3)-3-pentenyl methoxymethyl ether and a method for preparing (E3)-3-alkenyl acetate using the same. The (E3)-3-alkenyl acetate includes, for example, (E3,Z8,Z11)-3,8,11-tetradecatrienyl acetate and (E3,Z8)-3,8-tetradecadienyl acetate which are sex pheromone substances of tomato pest Tuta absoluta. 
2. Description of the Related Art
Tuta absoluta is a serious tomato pest. The larvae thrive inside tomato leaves, tomato fruits and the like which are not easily exposed to a chemical liquid. Accordingly, it is difficult to control them by using insecticides. In addition, because there is almost no natural enemy found in Europe recently attacked by the pest, the increased damage thereby cannot be stopped. Therefore, biological control methods are attracting attentions and use of a sex pheromone substance is expected as one of these methods.
As a main component of the sex pheromone composition of Tuta absoluta, (E3,Z8,Z11)-3,8,11-tetradecatrienyl acetate was identified (Attygalle et al. Bioorg. Med. Chem. 1996, 4(3): 305 to 314). Subsequently, (E3,Z8)-3,8-tetradecadienyl acetate was found as the second component and it was shown that a 10:1 weight ratio mixture of them had higher attraction effect than the main component alone (Svato{hacek over (s)} et al. J. Chem. Ecol. 1996, 22(4): 787-800).
Several new methods for synthesizing the sex pheromone substance are reported. For example, it is reported (J. N. Jham et al. Tetrahedron Lett. 1995, 36(31), 5471-5474) that the substance can be obtained by hydroaluminating (Z8,Z11)-8,11-tetradecadienyl-3-yl-1-ol with lithium aluminum hydride, followed by acetylation. It is also reported (A. L. Hungerf et al. J. Chem. Soc., Perk in Transl, 1998, 1839) that the substance can be obtained by subjecting tetrahydropyranyl-protected (Z8,Z11)-8,11-tetradecadienyl-3-yl-1-ol to Birch reduction to remove the tetrahydropyranyl group, followed by acetylation.